


Cockiness

by Robomantic



Category: Supernatural
Genre: Anal Sex, Bottom Dean, Burlesque, Fingerfucking, First Time, M/M, Rimming, Size Kink, Top Castiel, Underwear Kink, just a little comeplay
Language: English
Status: Completed
Published: 2013-01-24
Updated: 2013-01-24
Packaged: 2017-11-26 18:54:32
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 7,540
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/653373
Author URL: https://archiveofourown.org/users/Robomantic/pseuds/Robomantic
Summary: <blockquote class="userstuff">
              <p>Dean didn’t usually come to this kind of place, but Sam had given him the puppy dog eyes and argued and pleaded and even bribed him with pie.  He was seeing some new girl who apparently very into the alternative burlesque scene and she had invited them to come see a show on her night off.  </p><p>Aka: The one where Dean sees his first burlesque show, learns that male burlesque performers are a thing,  and tries a lot of new (sexual) things.  Also my Castiel underwear kink makes an appearance because I'm weakkkk.</p>
            </blockquote>





	Cockiness

**Author's Note:**

> Basically, I was listening to the song [Cockiness](http://www.youtube.com/watch?v=mbJRVufEX00) by Rihanna and had this whole imaginary Castiel strip tease going through my head and this was born. I have no idea why or how this popped into my head, but there you go. It's out in the world now. 
> 
> Unbeta'd as usual, so forgive my mistakes (I do my best once over, but I'm prone to miss things). Comments and con-crit are always welcome!

Dean didn’t usually come to this kind of place, but Sam had given him the puppy dog eyes and argued and pleaded and even bribed him with pie. He was seeing some new girl who apparently very into the alternative burlesque scene and she had invited them to come see a show on her night off. 

Dean was resistant at first. He had always been a fan of good old fashioned strippers and Sammy’s girlfriend had been quite adamant that burlesque was a whole different ball game. Dean liked his naughty entertainment to be a simple and uncomplicated. Give him a leggy brunette in a g-string and some Def Leppard and he was good to go. 

Still, Sammy persisted. He finally convinced Dean that there would still be hot chicks and booze (and that the first round would be on Sam) and Dean relented. He had never been able to turn down chicks and free booze.

Dean followed Sam and his girlfriend, Kayla (or Zephyr, as she was known on the stage) into a small club in the “hip” part of town. In other words, there was too little parking, too many people riding bikes, and the coffee and booze was too expensive. 

The inside of the club was small and intimate and all done up in red velvet and Victorian looking accents. There was a low stage at the far end of the club and small clusters of tables and chairs were scattered around the room. A long wooden bar took up one wall of the club and the whole place was lit by a large chandelier and red and black candles at all the tables. The bartenders were girls in Bettie Page haircuts and guys with curled mustaches and gauged out ears. 

Almost everyone in the club seemed decorated in all kinds of incredible tattoos and piercings. Dean’s only tattoo was a small pentagram design beneath his left clavicle that he had gotten along with Sam in memory of their father. In comparison the rest of the crowd he was feeling a little inadequate in the body art category, truth be told. 

All in all, it wasn’t too far from what Dean expected. Lots of hipsters.

Sam and Dean sat down at one of the tables toward the front while Kayla went over to the bar to say hello to a friend and grab some drinks. 

“See Dean, not bad right?” Sam said gesturing vaguely around the room.

“Yeah, the show hasn’t even started yet Sam. Hell, we haven’t even gotten our drinks yet.” 

“Come on Dean, you’re gonna love it. Just relax. You need to try new things every once in a while, man. You’re either at the shop or drinking in your apartment anymore. It’s getting kinda sad.” Sam said.

“Gee, thanks Sammy.” Dean said rolling his eyes, “What would I do with you? Rot in my recliner, I guess.” Dean said, but before Sam could think up a retort Kayla had returned with three drinks.

“Old fashioned’s courtesy of my friend Mandy!” she said cheerfully, setting a glass down in front of each of them. 

Kayla seemed to be a pretty great girl. She was a cute little thing with a scattering of brightly colored tattoos and a short blonde pixie cut. Apparently she was a gymnast for most of her life and did a lot of really intense stunts in her routines, based on what Sam had told him. She was cheerful and sweet and Dean could understand what Sam saw in her. Plus… free booze was one of the quickest ways to win Dean’s approval.

“Well cheers to your friend Mandy then!” Dean said before taking a swig of his drink. 

The already dim light from the chandelier went a little darker and a spotlight hit the stage. The emcee welcomed the crowd to the club and announced the opening act. She went by the name Kali. 

The girl that glided onto the stage had dark olive skin with wavy black hair. She had a look about her that was fierce and a little scary. Her act was a beautiful dance, sensuous and serpentine, like belly dancing in slow motion. The music was strange and ethereal and when Dean asked what it was, Sam said it was a band called Sigur Ros. 

Kayla explained that Kali had a boyfriend that was some kind of Icelandic or Swedish or god knows what. He was even named after one of those Norse gods, hence the weird Icelandic music, apparently. 

The next act was a super cute curvy little chick straight out of a pinup whose stage name was Ava Voom (Dean already thought she was awesome based on the name alone). Her act was a little closer to what Dean imagined when he heard the word burlesque. It was very retro and flirtatious and fun and Sam caught him smiling in enjoyment.

“See Dean, told you you’d like it! Pretty great, right?” he said. Dean just shrugged and nodded and went back to watching the show. 

The next girl on stage went by the name of Mistress Meg. She had a heart shaped face and curly hair and somehow managed to give off this vibe like she was patronizing the entire audience throughout her whole performance. She did a very scary hot demon themed thing that involved swinging around these balls of fire on chains. Kayla said it was called, “poi”. Dean was impressed and even a little disappointed when the song finished. 

The crew came out to clear the stage and set up for the next performer. Dean was a little surprised when all they brought out was a simple wooden chair and a small table with a stereo on it. The other performers had definitely put more thought and effort into their set and props than this. Suddenly the emcee’s voice was wafting over the quiet conversation of the audience.

“We have quite a treat for you lovely people tonight. Our very own first gentleman of burlesque is here to perform for you. Please give your warmest welcome to Castiel!” 

“Gentleman?” Dean said, quirking an eyebrow at Kayla. 

“Oh yeah! We have guys perform too. Not often, but yeah. Castiel’s excellent!” Kayla gushed. Dean furrowed his brow. He wasn’t exactly sure what to expect and he was a little uncomfortable with the idea of watching a dude strip or something. 

The spotlight hit the stage and a guy stumbled into the light. He looked downright lost. He had dark messy hair, bright half hooded eyes, and a helluva pout. He was wearing a dark rumpled suit with an oversized tan trench coat over it. It almost looked like someone had just yanked him off the street and thrown him onstage. 

The guy, Castiel, ran his hand through his hair and slumped down in the chair like he was exhausted, looking every bit the picture of a guy coming home from a long day of work and acting as though the crowd wasn’t even there. Dean’s curiosity was peaked. 

Castiel reached over and made a motion to flick on the stereo and suddenly the club was flooded with the sounds of some cheesy easy listening. Castiel slumped back in his seat for a second before kicking off his shoes and socks then he straightened up and looked around like he was making sure he was alone. He leaned over and fiddled with the radio again and suddenly the music was very different. 

It sounded like someone making a drumroll noise and then the beat hit hard and heavy and raunchy. 

_‘Suck my cockiness, lick my persuasion.’_

Castiel was up and moving slowly to the pounding beat. He dropped his coat off his shoulders and now his movements were a little clearer, his body rolling sensuously to the beat. Dean had planned to be appropriately disinterested the moment he heard there would be a male act, but he couldn’t look away.

_‘I want you to be my sex slave, anything that I desire.’_

The contrast of the whole overworked tax accountant thing with the incredibly sexual way the guy was moving and the dirtiness of the music was blowing Dean’s mind a little. He supposed that was the point. 

Even Sam was staring at the stage, his mouth hanging open. Dean felt a little better about himself at that, but he couldn’t deny the slow steady burn of arousal in his stomach as he watched the performance.

Castiel loosened his tie and, for a moment, Dean thought he was staring right at him, a hungry look in his eyes as he went to unbutton his white shirt, his fingers sliding down his exposed torso like he was teasing himself. He arched back in the chair as his fingers skirted along the waist of his pants and Dean’s breath caught in his throat. 

Fuck. Dean was having a crisis of sexuality.

Dean had found a guy attractive every now and then, maybe even thought about what it would be like to be with one, but it had never been more than a passing interest. He always wrote it off as healthy curiosity. 

This was a little harder to write off as curiosity. Literally harder. Harder as in standing up at that exact moment would be embarrassing as all hell. 

Castiel slid his shirt off his shoulders and let it fall next to the rest of his discarded clothes. Dean was surprised at how pleased he was that Castiel had kept the tie on. 

Now Castiel was standing up and undulating his hips as he undid the button of his pants, turning around as he slowly pulled his pants down to give the audience a view of his perfect ass clad in a pair of ridiculously clingy baby blue lace shorts. 

Lace for fuck’s sake. 

“Sonofabitch…” Dean muttered. Sam didn’t seem to hear him, but Kayla turned and cocked an eyebrow at him. Dean ignored her and the hot flush rising in his cheeks and kept watching the show. 

Castiel’s body was lean and lightly tanned. He had a body like a runner or a swimmer. Dean found himself staring at the indents of his hips leading right down to the considerable bulge in those ridiculous lace shorts. He must have had something else on underneath them to keep them from being way too revealing and Dean was now dealing with the fact that not only was he rock hard for a dude, but he was apparently way into lace. 

He was trying to will away his erection, but it seemed like Castiel’s every movement was designed to remind him of sex, his body rolling and arching in all the right ways. 

The music ended and suddenly the lights went up on the audience. Castiel gave the audience a look of pure embarassment, grabbed his trench coat to hide behind and sidled off the stage, an adorably shy smile on his face. Dean couldn’t help letting out an embarrassingly loud bark of laughter at the finale to Castiel’s performance. Apparently he was hot and hilarious to boot. Safe to say, Dean had a bit of a crush on the guy. 

The crowd applauded and many were even giving Castiel a standing ovation. Dean would have joined them, but he was still in no fit state to be standing. Instead he just clapped and whistled extra loud to make up for it. 

“So, I take it you liked Castiel’s performance?” Sam said laughing a little at Dean’s over-exuberant applause.

“What? It was… it was a cool concept. Creative.” Dean said trying to will away the blush reddening his cheeks. 

“Yeah, yeah. Definitely.” Sam said, but he was exchanging conspiratorial looks with Kayla that made Dean more than a little nervous. 

The final act of the night was apparently a pretty big name in the burlesque world, but Dean was paying no attention at that point. He was still trying to wrap his mind around his reaction to Castiel’s performance. 

He kept remembering the way Castiel looked in those blue lace underwear with the darker blue tie still hanging loosely around his neck. Why the hell was that so hot? It was kind of… odd. The whole performance had been odd, but in a decidedly awesome way. 

Suddenly everyone was applauding and he belatedly joined in, realizing that he hadn’t watched a single moment of the last act. 

People were slowly standing up and heading to the exits now that the lights were back up. Sam and Dean finished their drinks as Kayla went to say goodbye to some people. By the time she got back they were both shrugging into their jackets.

“Hey, some friends of mine are going to the bar next door for a couple drinks. You should come with. I can introduce you guys to my friends.” Kayla said. Dean hadn’t realized he was included in the invitation until he heard the words, ‘you guys’. 

“Why not? Dean, you coming?” Sam said, nudging Dean in the rib with his elbow. 

“Yeah, sure.” Dean said. He wasn’t going to say no to a stiff drink. He could certainly use one. 

They headed to the little hole in the wall bar next door and found an open table while Sam headed off to get them a round of beers. 

The familiar boozy sweaty smell of a bar and the cacophony of people talking and music playing had Dean feeling right at home. Bars like this were familiar to him. He felt a lot more in his element than he had at the club. 

Dean was shaken out of his moment of zen by Kayla shouting across the bar.

“Castiel! Over here!” she yelled and Dean looked in the direction of her shouting. 

Yup. He was fucked. 

Castiel had apparently just walked in. He was dressed in faded jeans and a clingy threadbare tee shirt that made it impossible for Dean to not think of the body underneath it. He already had his coat off and thrown over his arm and Dean was amused to see that it was the same tan trench coat he had worn in his act. 

Castiel smiled and started heading toward their table. Dean’s heart was beating like a drum and he was more than a little embarrassed that this guy had him wound up like he was an awkward horny teenager on a first date. 

_‘Chill out, Winchester.’_ He thought to himself as Castiel took the chair right next to him. 

“You were awesome tonight!” Kayla gushed. Castiel just smiled and blushed a little. 

Freakin’ adorable. 

“Yeah, you were great.” Dean added and suddenly Castiel’s smile was on him and he was looking right into Dean’s eyes with laser-like focus.

Now that they were closer Dean saw that Castiel’s eyes were insanely blue, even in the smoky light of the bar. Blue like the lacy… No, Dean was not following that train of thought. That way madness lay.

“Thank you.” Castiel said and Dean felt those words travel through his body like a shock wave. Fuck, he had a hot voice. It was deep and kind of rough in a way that Dean thought was usually reserved for the bedroom, almost growly. 

Dean smiled at Cas as Sam arrived at the table, beers in hand. Sam was giving him a strange look and Dean didn’t understand why until he realized he had been giving Castiel that smile. His patented charm the pants off of anyone with a pulse smile. Sam was familiar with it, having watched Dean woo countless chicks with it back when they both spent way too much time together. 

“Oh, I should do introductions!” Kayla said, and Dean felt a wave of relief at the distraction.

“This is my boyfriend Sam and that’s his brother, Dean. Guys, this is Castiel.” Kayla said with a smile.

“So what’s your real name, Castiel?” Dean said, trying (and failing) to not be flirtatious.

“Actually my real name is Castiel. No one ever believes me, though so I just tell people my real name is Jimmy.” Castiel said and Dean chuckled. 

“So why didn’t you just tell me your name was Jimmy then?” Dean asked.

“I don’t say that to people I might actually see again. It would be awkard if you ended up calling me Jimmy later.” Castiel said, never breaking eye contact. It was a little unnerving and oddly sexy the way he stared like that, like he was staring right into Dean’s thoughts. 

“So you plan on seeing me again then?” Dean said with a decidedly wolfish grin. Yes, this was without a doubt flirting. Dean had apparently decided to dive right off the deep end with this one. For his first time flirting with a dude, it seemed to be going shockingly well. 

Dean belatedly realized that he had no idea if this guy was even into guys, much less Dean, but he had pretty good instincts when it came to flirting. He decided to trust his instincts on this one.

“That depends on how nice you are. I just met you, after all.” Castiel replied with a grin that bordered on devious. Holy hell, this was full on flirting. Score one Dean’s instincts. 

“Well how about I start by getting you a drink? That’s a nice gesture right?” Dean said. 

“Whatever you’re having’s fine with me.” Cas replied with a smile. Dean got up to head to the bar and suddenly remembered that they were not alone. Kayla was giggling like a school girl and Sam’s eyebrows seemed to have found a permanent home near his hairline. Dean almost laughed out loud at the shocked look on his brother’s face, but instead he just smiled and gave Sam an almost imperceptible shrug as he went to grab Castiel a beer. 

Dean fought his way through the steadily growing crowd at the bar to get Castiel a drink. He finally managed to get the attention of one of the bartenders and headed back to the table. He sat the beer in front of Castiel without interrupting the conversation he was now having with Sam.

“Castiel’s an interesting name, does it mean anything?” Sam said.

“My parents are very religious. They named my siblings and me after angels. Castiel is the angel of Thursday and I was born on a Thursday so…” he finished with a shrug.

“Castiel does this awesome warrior angel routine with wings and a sword and everything. It’s pretty amazing.” Kayla said.

“I’d like to see that.” Dean said and Castiel’s eyes were on his again as he wrapped his lips around the bottle to take a drink. 

Dean was very keenly aware that to the outside observer they were eye banging the hell out of each other and he found he didn’t really mind as much as he might have at the beginning of that night.

“Sooo….” Sam said breaking the awkward silence before Dean took up the slack.

“So Cas, you have a lot of siblings then?” Dean asked, helpfully veering the conversation somewhere safer for the sake of his brother. 

“Cas?” Castiel said, tilting his head slightly.

“Shit, sorry. It’s just Castiel’s kind of a mouthful.” Dean said and he couldn’t help the wolfish grin that spread across his face when he realized what he had said. 

“Yeah, I would say so.” Cas said with an equally devious grin. 

“Um, why do I feel like I shouldn’t be here right now?” Sam said and Kayla very obviously elbowed him in the side.

“Because you were going to come meet some more of my friends, right?” Kayla said, doing a piss-poor job of not being incredibly obvious. 

“Yeah! Right, right. Well it was nice meeting you.” Sam said to Cas before going off to follow Kayla.

“Nice to meet you too, Sam.” Cas said, finally breaking his gaze from Dean.

“Well that was awkward.” Dean said with a chuckle once the two of them were left alone.

“Was it?” Cas asked as though he genuinely hadn’t noticed. Dean just shook his head and smiled. 

They talked as they nursed their beers, leaning close to hear each other over the din of the bar. Cas talked about his crazy family and Dean talked about his. Cas told Dean about his day job working at a book store and Dean talked about working as a mechanic and his beloved Impala. Dean was surprised when Cas told him that he’d actually been in the army for several years.

This went on for a while and Dean noticed that they had both finished their beer and neither had even mentioned getting another one.

“So did you really like my act?” Castiel asked him and he looked so adorably unsure, like he was genuinely worried about whether Dean liked the show or not. Dean was totally thrown off his game for a moment. 

“Yeah, dude! You were amazing. Honestly, that was my first time going to a burlesque show and I didn’t really expect to see a guy perform, but it was awesome. I umm… I especially liked the…” Dean trailed off. Despite the fact that he had been a total cocky flirt only moments ago, he felt himself flushing at the thought of Castiel stripped down and exposed in the spot light, his ass hugged tight by baby blue lace.

“Well I’m glad you liked it.” Cas said, and bless him for not making Dean finish that sentence.

“Can I be honest with you, Dean?” Castiel said, leaning in close enough that Dean could smell him, clean and fresh like sandalwood and vanilla with something darker and spicier underneath it. 

“Sure.” Dean said.

“I really want to take you home tonight. In fact, I kind of want to leave here right now, but I don’t want to make you uncomfortable.” Cas said and Dean’s eyes widened before he finally let out a laugh.

“You’re something else, dude.” He said.

“Sorry. I’m too forward.” Cas said, looking a little crestfallen.

“No, no! It’s actually kind of awesome. And… I want you to take me home, but…” Dean said, trailing off, a little embarrassed.

“But?” 

“But I’ve… umm I’ve never actually been with a guy before and there’s a pretty big chance I might suck at it.” He said. Castiel just smiled.

“Some sucking is to be expected, Dean.” He said with a warm smile and Dean already felt himself relax. Castiel seemed to bounce back and forth between being disarmingly sweet and adorable and a little intimidating and predatory, sometimes landing somewhere in the middle. Dean didn’t mind. He kind of liked being kept on his toes a little.

“Then I guess, let’s get out of here?” Dean said and his heart sped up again. This was actually happening. What the hell was he doing? He was half wondering if Castiel’s dancing was some form of seductive hypnosis as he followed him out the door. They were moving crazy fast, but he didn’t want it to stop. 

He realized he hadn’t even said goodbye to Sam and Kayla, but he had the feeling they could guess pretty well where he’d gotten off to. 

Apparently Cas’s apartment was pretty close by so they walked the block or so over. Dean slid his hand under Cas’s trench coat and put his hand on the small of his back as they walked. Cas bit his lip and in an instant he had Dean up against a brick wall, kissing him and pressing his arms up against the brick.

Cas was stronger than he looked. Dean had the strangest urge to see just how strong he was. He wondered if he could hold him up against the wall and… well, that was an interesting thought. 

Dean hadn’t realized that was something he wanted until that moment. He had never really been the dominant type in bed, despite his outer machismo and cockiness. With women it was different though. He was the one doing the fucking, even if the chick was in charge. He had never thought he’d want to be the one getting fucked before. 

Cas kept his arms pinned as he worked his way across Dean’s jaw, scraping his teeth gently at his stubble. He bit down gently when he reached the crook of Dean’s neck and it was all Dean could do to lean in to Cas, desperate for more contact. Cas obliged him by pressing his hips into Dean and the pressure against his cock made him realize just how hard he was and that, even better, he wasn’t the only one.

“Fuck, Cas. You have to get me indoors right now or we’re going to get arrested for public indecency or something.” Dean said. It was kind of hard to form a full sentence with Cas licking and sucking at his neck like some kind of sexy vampire, but he managed.

“Come on.” Cas said, finally letting go and pulling Dean down the street and up a flight of stairs to his apartment. Apparently Cas lived above some trendy thrift store in a small, but fairly cozy one room apartment.

Dean didn’t see much of the interior, however, as the moment he got in the door Cas was on him again, dragging him towards his bedroom as he kissed him. They managed to only knock over a couple of things before they managed to collapse backwards into Cas’s bed. 

Dean was suddenly nervous all over again. He had no idea what he was doing, all he knew was that he wanted. He didn’t realize he had frozen up until he realized Cas was giving him a concerned look, head tilted in that adorable way.

“Are you alright, Dean?” 

“Yeah, I’m just… nervous?” Dean said with a chuckle. 

“Just relax. We don’t have to do anything you don’t want to. Let me take care of you.” Castiel said and he sounded so genuine that Dean couldn’t help trusting him. 

Dean slid his hands under Cas’s shirt to show him that he wanted to keep going. He let his fingers map out the smooth warm expanse of skin like he’d imagined doing since the performance earlier. Dean had wanted to touch him so bad as he had watched him and now that he had his chance he wanted to take his time. 

He pulled the shirt up and Cas lifted his arms so Dean could pull it over his head and throw it to the side. He took a second to take in the view now that he had Cas up close and all to himself. 

He leaned forward and started kissing and nibbling a trail from Cas’s neck, down to his collar bone before tracing his tongue gently over a nipple. Cas let out a quiet gasp and arched his back at the touch and Dean took that a sign to keep going. 

Dean decided to experiment by biting down gently on Cas’s nipple and was rewarded by Cas moaning and grasping at Dean’s short hair. Dean went for Cas’s mouth again, biting gently at those plush lips as his thumbs slid down the valleys of Cas’s hips.

Cas broke the kiss long enough to push Dean down onto his back and Dean felt a little rush at the way Cas was man handling him. He couldn’t remember taking off his jacket, he assumed he lost it somewhere between the apartment door and the bedroom, but now Castiel was working on getting his shirt off of him too.

He sat up enough for Cas to pull his shirt over his head. Cas slid down the length of Dean’s body, looking up at him with an eager glint in his eye as his hands trailed down to unbutton Dean’s jeans. 

“Is this okay?” Cas asked, looking up at Dean through his eyelashes.

“Hell yes.” Dean growled as Cas cupped his hand around his cock through his jeans. Dean lifted his hips and let Cas pull his jeans and boxer briefs off in one solid movement. 

Cas was looking at Dean’s cock like a kid with a Christmas present and Dean felt like his skin was too hot under Cas’s lustful gaze. 

“Already so wet for me.” Cas said, in awe as he gripped Dean and slid his thumb across head of his cock and the mess of precum there. Dean couldn’t stop staring as Cas licked the wetness from his thumb before taking the head of his cock into his mouth to give it the same treatment. 

The way he sucked and licked at Dean’s cock felt almost worshipful. Dean had always said that the best blowjobs came from people that genuinely enjoyed sucking cock. It seemed that Cas was definitely one of those people. 

Cas had no shame in the way he sucked at him hungrily, taking in every inch until Dean could feel the back of his throat. He wasn’t afraid to get sloppy either, pulling off Dean with a wet pop and rubbing the slippery wetness of the head over his lips like a balm. 

Dean hips canted up towards Cas’s mouth, but he pressed Dean back into the bed with one arm. He was completely in control of Dean’s pleasure and Dean liked it.

“Holy fuck, Cas.” Dean panted. Cas took him back into his mouth and started bobbing on his cock, looking up into Dean’s eyes as he did. 

“Shit, you can’t… I’m gonna come if you don’t stop.” Dean said. Cas pulled away with a filthy slurping noise that made Dean want to beg him to keep going, but he was determined not to come yet so he resisted.

Cas’s lips were wet and swollen and Dean needed to taste them, taste himself in Cas’s mouth. He pulled him into a kiss and chased the taste of himself on Cas’s tongue.

“Tell me what you want, Dean.” Cas said as he pulled away from Dean’s mouth. Dean felt a shiver run down his spine at the sound of his name in Cas’s voice, rough and dirty. 

“I want… I want you to fuck me, Cas.” Dean said. He was more than a little nervous and had basically no idea what to expect, but the thought of Cas taking him like that, filling him up from the inside, was driving him crazy. He needed to know what it was like and despite the fact that he had just met him, he trusted Cas to show him. 

“Are you sure?” Cas asked him.

“Yeah. I’m sure. If you want to, I mean.” Dean said and Cas smiled in a way that made it very clear he was hoping for that exact answer. 

“Dean, I’ve been thinking about fucking you since the moment I met you. You have no idea how much I want to.” He said into Dean’s ear and Dean couldn’t help shudder in anticipation at those words. 

“How do you want to do it?” Cas asked him.

“Can we do it like this?” Dean asked, reaching down to urge Castiel out of his jeans. 

“Yes, but it might be easier if you turned over.” 

“Don’t care. I want to watch you fuck me.” Dean said and Cas couldn’t argue with that. Instead he stood up to finish undressing and Dean pretended not to be disappointed when he saw that Cas wasn’t wearing the underwear from his show. 

Cas grabbed a condom and a bottle of lube from his dresser and when he turned around Dean had a mini heart attack.

It wasn’t as though he hadn’t noticed it earlier. After all, the lacy underwear hadn’t left too much to the imagination. Seeing him fully hard and up close, was a little different. He was a little intimidated.

Cas was big… like porn star big. Obscenely big, really. Dean was torn between wanting to lick it and wanting to run from the damn room. 

Cas must have noticed his apprehension. 

“You can change your mind. I mean I understand. I probably should have... told you first?” he said, blushing beet red. 

“Um, it’s okay. I want to try, just… take it slow?” Dean said, but inside his head was a steady chorus of _‘fuckfuckfuckfuckfuckfuck’_ and _’What the hell have I gotten myself into?’_

“How about you turn over at first and if that works okay, then we’ll do it face to face?” Cas said. His voice had gone soft like he was speaking to a spooked horse or something. Dean wondered just how freaked out he had looked. 

“Yeah, okay.” Dean said.

“I’m going to use my tongue and my fingers first, is that okay?” Cas asked. 

“Umm, sure.” Dean said. It seemed this night was going to be full of new experiences. He turned over on the bed and Cas started by rubbing his back and kissing the back of his neck gently until he relaxed. Dean felt a rush of excitement and as Cas’s cock pressed into his thigh. He couldn’t believe he was going to let Cas put that inside him. 

Maybe. 

Maybe he would get as far as fingers and change his mind. 

Cas moved down to his ass and gently kneaded his ass cheeks and Dean moaned a little. He had always liked it when girls squeezed his ass while he fucked them so he wasn’t really surprised that he liked what Castiel was doing. 

Cas spread him open and Dean gasped as he felt warm breath against his hole. Cas started licking soft and wet at his taint and worked his way up. He had Dean moaning into the pillow before he even got to his hole and Dean startled himself by thrusting his hips up a little as Cas finally lapped at his hole. 

Dean really had no idea how he’d gone his whole life without experiencing rimming. 

Cas kept Dean’s hips pressed firmly into the mattress with his palm on the small of his back as he fucked into Dean’s hole with his tongue. Dean was moaning and crying out to the point that he was downright embarrassed as Cas licked at him and even dragged his teeth across the sensitive flesh there. It felt dirty and wrong in the best possible way. 

Cas lubed up a finger and let it take the place of his tongue, pressing in up to the first knuckle as he still kissed and nibbled at the curve of Dean’s ass.

“Spread yourself for me, Dean. I want to see you.” Cas said in that fucking voice of his and Dean couldn’t help obeying. He reached back and held himself open for Cas.

“So good, just like that. I wish you could see yourself, how perfect you look like this.” Cas said, his voice barely above a growl. Dean just moaned into the pillow.

“Keep talking, please.” He panted, turning his head enough to see Cas out of the corner of his eye. Cas obliged him.

“I could do this for hours. Just watch you open up for me, take whatever I give you. The way you moan when I touch you. Can’t even imagine what fucking you will be like.” Cas said, sliding his finger in deeper. Cas slid his finger all the way in and started fucking in and out slowly. Dean tried desperately to buck his hips into it, but Cas held him firmly in place. 

When the single finger seemed to slide in an out to Cas’s liking he removed and added more lube to his fingers.

“Are you ready for another finger?” he asked. 

“Yes.” Dean moaned eagerly. He realized that the way Cas was holding him down also meant that he couldn’t really rub himself against the sheets and the slow patient way Cas was teasing him was driving him insane.

Cas slid in two fingers and Dean did his best to relax as his hole stretched a little further. Cas was going slow enough that it didn’t really hurt yet, more strange and unfamiliar than anything else. 

“So perfect and tight.” Cas murmured and Dean could feel the heat of his gaze on his exposed ass. It was intense and a little dizzying. 

When Cas added a third finger Dean started to feel the burn in the stretch and he reveled in it. Then Cas pressed in and crooked his fingers just right and Dean felt like the breath had been knocked out of him.

“Cas, there. Right there. I need…” Dean babbled.

“Shh, I know what you need.” Cas said and Dean practically whimpered. Cas’s fingers kept brushing up against his prostate until he was begging Cas for more. 

“Do you want my cock now, Dean?” Cas whispered in his ear.

“Yeah, Cas. Do it.” Dean said. He groaned as Cas removed his fingers to put on the condom and slick up his cock with what was probably an obscene amount of lube. 

He gripped Dean’s hips and pulled him up onto his hands and knees. Dean’s almost laughed when he realized that his thighs already felt weak. Probably from pushing up against Cas as he held his hips down.

God, he’d barely even realized he’d been doing it. Was he really that eager? There was a wet spot on the bed where Dean’s cock had leaked onto the sheets that proved that yes, he was.

Cas pulled him up further until his back was flush with Cas’s chest. He lined up his cock with Dean’s wet and eager hole and Dean shivered a little at the slow and steady pressure. Cas kissed and bit at the back of his neck and reached forward to stroke Dean’s cock as he pushed in, slow and steady.

The sudden pleasure of his cock finally receiving some much needed attention helped take the edge off the intense pressure and dull burning feeling as Cas pressed in.

“Relax Dean, you have to relax. You’re so tight, so tight for me.” Cas said, his voice trembling as he willed himself to stay still and wait for Dean to relax.

Dean breathed deep and focused on Cas’s hand around his cock. He’d gone a little soft at first, but as he got used to the stretch a little more he started to harden again. Cas felt him relax and started sliding in deeper. 

“Jesus fucking Christ Cas, you’re so big.” Dean moaned, his eyes watering a little. He felt full, he felt like his body might break apart from how full he was and he could feel the heat of Cas inside him. He could almost feel his pulse there, but he may have been imagining that. It was a little overwhelming, considering his experience in being on the receiving end of anal sex up to this point had been zilch. 

“You can take it Dean, I know you can take it. Feel good?” Cas said and as he asked he thrust forward just so and hit that spot that made Dean feel like he was out of his body for a moment. 

“Fuck, yes. Keep going Cas.” Dean moaned, pressing back into Cas’s thick cock. Castiel pushed him forward so he was leaning on his elbows again and drew out slowly, almost all the way out, before thrusting in again. Dean shouted out a colorful slew of curse words interspersed with pleas of harder and more and deeper and Cas’s name said over and over, like a prayer. 

Cas’s hands gripped Dean’s hips tight as he gave in to Dean’s pleas and pounded into him, deep and steady. Dean would have reached down to touch himself, but he was using both arms to brace himself against the headboard. 

Cas pulled out without warning and Dean cursed at him. Cas ignored him and turned him over on his back and Dean finally got to look at Cas for the first time since he’d started fucking him. 

His body was glistening with the sweat of his exertion and the look on his face was hungry, predatory really. His deep blue eyes were almost all pupil and it was obvious that he’d been biting his lip nearly the whole time. He was gripping the base of his cock tight and Dean realized he was holding back from coming. 

“Give me a second Dean. I’m so damn close.” He growled, closing his eyes like looking at Dean might just send him over the edge. He waited for a moment and Dean caught his breath, taking a moment to enjoy the sight of a completely fucked out Castiel. 

He had a feeling that seeing Cas perform again would be an entirely different experience after this. He’d be lucky if he could get through it without coming in his pants. 

Cas leaned forward and kissed Dean slow and passionate as he lined himself up again and pushed back into Dean’s slick and well used hole. Dean moaned into the kiss as Cas rolled his hips forward in a few slow thrusts. He leaned back so he could look down at his cock sliding in and out of Dean and let out a low groan. 

“That’s just beautiful. So stretched out for me, Dean. You should see the way you look right now. You’re gorgeous like this, all spread out for me.” Cas said. He hitched Dean’s legs up over his elbows and pulled him in harder. Dean’s cock was leaking against his stomach and he felt like he was either going to come or die soon. He wasn’t sure which. It wasn’t hard for Cas to guess to tell how close he was.

“Do you think you can come for me, Dean? Can you come for me like that, with my cock in your ass?” Cas said and instead of waiting for an answer he pulled Dean in by his hips at just the right angle and started mercilessly hitting his prostate. 

Dean didn’t even have the presence of mind to touch himself before he his orgasm hit him like Mack truck. He almost blacked out for a second as his come painted hot stripes over his stomach and chest. He could feel himself clenching tight around Cas’s cock as he rode out his orgasm. 

Cas held off until Dean finally stilled, but the moment he did he pulled out and yanked off the condom. He jerked himself a couple of times before he came in hot spurts all over Dean. The better part of it soaked Dean’s cock and stomach, but some of it managed to shoot all the way to Dean’s cheek. 

Apparently Dean was very into the money shot because he felt his cock twitch in a valiant effort to get hard again as he surveyed the mess Cas had made of him. 

Cas leaned forward and wiped the come from Dean’s cheek with his thumb, but before he could pull it away Dean caught him by the wrist and sucked his thumb into his mouth, licking it clean. 

Cas hummed in approval and smiled. Dean kind of liked the taste of Cas, salty and bitter and almost sweet at the same time. He slid a finger through the mess on his stomach and licked it off again, this time tasting himself mixed in with Cas. 

“Dean, you have to stop. You’re going to kill me.” Cas groaned and Dean just chuckled. Cas got up and headed to the bathroom before coming back with a wet cloth. 

Dean went to take it from him to clean up, but Cas just ignored him and went about cleaning Dean up with a gentleness that made Dean’s heart hurt. 

It was quite possible that he was overwhelmed with warm fuzzy afterglow feelings because he was more than a little relieved when Cas finally collapsed next to him on the bed. 

He had been waiting for Cas to shoo him out onto the street or something, honestly. He’d been on the other end of one night stands enough times that it would have been karma if he had. 

“I think you should come see my next performance. If you want to, I mean.” Cas said, leaning his head against against Dean’s chest.

“Yeah, I definitely want to. Especially if this is how you celebrate your performances.” Dean said, absently running his hand through Cas’s sweat dampened hair.

“I also think you should go out with me. Tomorrow. For breakfast.” Castiel said before looking up at Dean to gauge his response. How he went from fucking Dean through the mattress to being so cute and innocent looking, Dean really didn’t know. 

“Sounds like a plan, but there’s only one problem.” Dean said. Castiel tilted his head and furrowed his brow.

“I don’t know if I’m going to be able to walk tomorrow.” Dean said. 

“You’re right. Maybe I’ll order in then.” Castiel replied and the look on his face was so serious and genuinely concerned that Dean almost choked from trying not to laugh.

“Yeah, I think that would be best.” Dean finally said before rolling over to kiss Cas again. 

Dean couldn’t help laughing to himself a little when he remembered something Sammy had said earlier in the night.

_‘You need to try new things every once in a while, man.’_

Sometimes Sammy’s advice wasn’t half bad.

**Author's Note:**

> Check out [my tumblr](http://cultofcastiel.tumblr.com/) over here. Pretty much a Teen Wolf and Supernatural fandom blog, if you're into that sorta thing :)


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